HCID 59543137, compound → 4-{[tert-Butyl(dimethyl)silyl]oxy}-3-fluorocyclohexanamine

HRID 1970989Notes

Reaction equation

HRID 1970989 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][CH:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:6]([F:18])[CH2:5]1)=[N+]=[N-]>CO.[Pd]>[Si:11]([O:10][CH:7]1[CH2:8][CH2:9][CH:4]([NH2:1])[CH2:5][CH:6]1[F:18])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

4

Reactant 1

HCID 59543137HCID 59543137, compound

Product 1

HCID 595431224-{[tert-Butyl(dimethyl)silyl]oxy}-3-fluorocyclohexanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred solution [(4-azido-2-fluorocyclohexyl)oxy](tert-butyl)dimethylsilane (1.0 g, 3.66 mmol) in MeOH (15 mL) was added Pd/C in MeOH. The flask was evacuated and filled with hydrogen several times, and left to stir overnight under hydrogen atmosphere. The mixture was diluted with DCM, filtered through a pad of Celite, and concentrated to afford the title compound.

Workup

  1. customThe flask was evacuated
  2. additionfilled with hydrogen several times
  3. waitleft
  4. additionThe mixture was diluted with DCM
  5. filtrationfiltered through a pad of Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bae95b7b94349f9b70c918431b8eece
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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